Ethanol → HCID 54146711, compound

HRID 1743041Notes

Reaction equation

HRID 1743041 reaction equation
[N+:1]([C:4]1[N:5]([CH2:9][C@@H:10]2[CH2:12][O:11]2)[CH:6]=[CH:7][N:8]=1)([O-:3])=[O:2].C(O)C.C([N:18]([CH2:21][CH3:22])CC)C>>[N:18]1([CH2:12][C@H:10]([OH:11])[CH2:9][N:5]2[CH:6]=[CH:7][N:8]=[C:4]2[N+:1]([O-:3])=[O:2])[CH2:21][CH2:22]1

Participants

4

Reactant 3

HCID 702EthanolHCID 8471TriethylamineHCID 10986673HCID 10986673, compound

Product 1

HCID 54146711HCID 54146711, compound

Procedure

A solution of 0.3 g (1.8 mmole) of (R)-(+)-2-nitro-1-(2-oxiranylmethyl)-1H-imidazole, 0.24 g (5.4 mmole) of 1H-aziridine, and 3.5 mL of 99:1 absolute ethanol: triethylamine is heated at reflux for 10 minutes, cooled, and concentrated. The residue is crystallized from 99: 1 absolute ethanol:triethylamine to give 0.22 g of product, mp 118.5°-120° C. [α]D24 =+23.5° [c0.98, chloroform].

Workup

  1. temperatureat reflux for 10 minutes
  2. temperaturecooled
  3. concentrationconcentrated
  4. customThe residue is crystallized from 99: 1 absolute ethanol

Sources & evidence

ORD record
ord-291dc49bf50049189afb8b786ce02c40
Source dataset
uspto-grants-1994_08
Patent number
US05342959

Reaction notes

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